
Shelter Island Vacations from ₩596,806
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The Latest Shelter Island Vacation Packages

Royalton Park Avenue
Reviewed on Dec 14, 2025

The Fifth Avenue Hotel
Reviewed on Dec 13, 2025

Fouquet's New York
Reviewed on Oct 10, 2025

The Langham, New York, Fifth Avenue
Reviewed on Dec 15, 2025

Placemakr Wall Street
Reviewed on Dec 5, 2025
Where to stay in Shelter Island

Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa
Everything was perfect. Staff, room, experience. Will definitely stay again.
Reviewed on Dec 14, 2025

Water's Edge Resort & Spa
Holiday family tradition!
Reviewed on Dec 12, 2025

Pier Blue Inn Old Saybrook - Essex
Nice, pet friendly facility with an amazing Indian restaurant next door!
Reviewed on Dec 14, 2025
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
